Structure and charge transfer in binary ordered monolayers of two sulfur-containing donor molecules and TNAP on the Au(111) surface

Journal of Physical Chemistry C

Volumn 118, Issue 6, 2014, Pages 3035-3048

  Fiedler, Benjamin ^a   Reckien, Werner ^a   Bredow, Thomas ^a   Beck, Johannes ^a   Sokolowski, Moritz ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84894098659     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp407579z     Document Type: Article

References (41)

1. Dressel, M. Ordering Phenomena in Quasi-One-Dimensional Organic Conductors Naturwissenschaften 2007, 94, 527-541
2. Ferraris, J.; Cowan, D. O.; Walatka, V.; Perlstein, J. H. Electron Transfer in a New Highly Conducting Donor-Acceptor Complex J. Am. Chem. Soc. 1973, 95, 948-949
3. Schott, J. H.; Ward, M. D. Snapshots of Crystal Growth: Nanoclusters of Organic Conductors on Au(111) Surfaces J. Am. Chem. Soc. 1994, 116, 6806-6811
4. Fraxedas, J.; Caro, J.; Figueras, A.; Gorostiza, P.; Sanz, F. Surface Morphology of Grown Thin Films of the Quasi One-Dimensional Organic Conductor TTF-TCNQ Studied by Atomic Force Microscopy Surf. Sci. 1998, 395, 205-215
5. Fernandez-Torrente, I.; Franke, K. J.; Pascual, J. I. Vibrational Kondo Effect in Pure Organic Charge-Transfer Assemblies Phys. Rev. Lett. 2008, 101, 217203
6. Umbach, T. R.; Fernandez-Torrente, I.; Ladenthin, J. N.; Pascual, J. I.; Franke, K. J. Enhanced Charge Transfer in a Monolayer of the Organic Charge Transfer Complex TTF-TNAP on Au(111) J. Phys.: Condens. Matter 2012, 24, 354003
7. Gonzalez-Lakunza, N.; Fernandez-Torrente, I.; Franke, K. J.; Lorente, N.; Arnau, A.; Pascual, J. I. Formation of Dispersive Hybrid Bands at an Organic-Metal Interface Phys. Rev. Lett. 2008, 100, 156805
8. Fernandez-Torrente, I.; Kreikemeyer-Lorenzo, D.; Strozecka, A.; Franke, K. J.; Pascual, J. I. Gating the Charge State of Single Molecules by Local Electric Fields Phys. Rev. Lett. 2012, 108, 036801
9. Jäckel, F.; Perera, U. G. E.; Iancu, V.; Braun, K. F.; Koch, N.; Rabe, J. P.; Hla, S. W. Investigating Molecular Charge Transfer Complexes with a Low Temperature Scanning Tunneling Microscope Phys. Rev. Lett. 2008, 100, 126102
10. Braun, K. F.; Hla, S. W. Charge Transfer in the TCNQ-Sexithiophene Complex J. Chem. Phys. 2008, 129, 064707
11. Fernandez-Torrente, I.; Franke, K. J.; Pascual, J. I. Structure and Electronic Configuration of Tetracyanoquinodimethane Layers on a Au(111) Surface Int. J. Mass Spectrom. 2008, 277, 269-273
12. Fernandez-Torrente, I.; Monturet, S.; Franke, K. J.; Fraxedas, J.; Lorente, N.; Pascual, J. I. Long-Range Repulsive Interaction between Molecules on a Metal Surface Induced by Charge Transfer Phys. Rev. Lett. 2007, 99, 176103
13. Kanai, K.; Akaike, K.; Koyasu, K.; Sakai, K.; Nishi, T.; Kamizuru, Y.; Nishi, T.; Ouchi, Y.; Seki, K. Determination of Electron Affinity of Electron Accepting Molecules Appl. Phys. A: Mater. Sci. Process. 2009, 95, 309-313
14. Berger, P. A.; Dahm, D. J.; Johnson, G. R.; Miles, M. G.; Wilson, J. D. Structure, Conductivity, and Electron Spin Resonance of Tetrathiafulvalene 11,11,12,12-Tetracyanonaphtho-2, 6-quinodimethane (TTF)(TNAP) Phys. Rev. B 1975, 12, 4085-4089
15. Toyoda, J.; Oda, A.; Murata, I.; Kawamoto, A.; Tanaka, J. Crystal-Structure of an Alternated Stacking Charge-Transfer Complex of 2,7-Bis(methylthio)-1,6-dithiapyrene (MTDTPY) with Tetracyano-2,6- naphthoquinodimethane (TNAP) Bull. Chem. Soc. Jpn. 1993, 66, 2115-2117
16. Bechgaard, K.; Jacobsen, C. S.; Andersen, N. H. A New Organic Low Temperature Conductor: HMTSF-TNAP Solid State Commun. 1978, 25, 875-879
17. Diekmann, J.; Hertler, W. R.; Benson, R. E. Substituted Quinodimethans. VII. Substituent and Structural Effects in Cyano-Substituted Quinodimethans J. Org. Chem. 1963, 28, 2719-2724
18. Kiel, M.; Duncker, K.; Hagendorf, C.; Widdra, W. Molecular Structure and Chiral Separation in α-Sexithiophene Ultrathin Films on Au(111): Low-Energy Electron Diffraction and Scanning Tunneling Microscopy Phys. Rev. B 2007, 75, 195439
19. Höfer, A.; Duncker, K.; Kiel, M.; Wedekind, S.; Widdra, W. Adsorption of Sexithiophene on Au(001): Molecule-Induced Partial Lifting of the Substrate Reconstruction Phys. Rev. B 2011, 83, 075414
20. Ishii, H.; Sugiyama, K.; Yoshimura, D.; Ito, E.; Ouchi, Y.; Seki, K. Energy-Level Alignment at Model Interfaces of Organic Electroluminescent Devices Studied by UV Photoemission: Trend in the Deviation from the Traditional Way of Estimating the Interfacial Electronic Structures IEEE J. Sel. Top. Quantum Electron. 1998, 4, 24-33
21. Lichtenberger, D. L.; Johnston, R. L.; Hinkelmann, K.; Suzuki, T.; Wudl, F. Relative Electron Donor Strengths of Tetrathiafulvene Derivatives: Effects of Chemical Substitutions and the Molecular Environment from a Combined Photoelectron and Electrochemical Study J. Am. Chem. Soc. 1990, 112, 3302-3307
22. VandeVondele, J.; Lynden-Bell, R.; Meijer, E. J.; Sprik, M. Density Functional Theory Study of Tetrathiafulvalene and Thianthrene in Acetonitrile: Structure, Dynamics, and Redox Properties J. Phys. Chem. B 2005, 110, 3614-3623
23. Fiedler, B.; Rojo-Wiechel, E.; Klassen, J.; Simon, J.; Beck, J.; Sokolowski, M. Ordered Structures of Two Sulfur Containing Donor Molecules on the Au(111) Surface Surf. Sci. 2012, 606, 1855
24. Kilian, L.; Umbach, E.; Sokolowski, M. A Refined Structural Analysis of the PTCDA Monolayer on the Reconstructed Au(111) Surface-"Rigid or Distorted Carpet?" Surf. Sci. 2006, 600, 2633-2643
25. Corso, M.; Fernandez, L.; Schiller, F.; Ortega, J. E. Au(111)-Based Nanotemplates by Gd Alloying ACS Nano 2010, 4, 1603-1611
26. Guo, Q.; Fiedler, B.; Sokolowski, M. Unpublished work. 2012.
27. Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, C. Electronic Structure Calculations on Workstation Computers: The Program System Turbomole Chem. Phys. Lett. 1989, 162, 165-169
28. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
29. Schäfer, A.; Huber, C.; Ahlrichs, R. Fully Optimized Contracted Gaussian Basis Sets of Triple Zeta Valence Quality for Atoms Li to Kr J. Chem. Phys. 1994, 100, 5829-5835
30. Schaftenaar, G.; Noordik, J. H. Molden: A Pre- and Post-Processing Program for Molecular and Electronic Structures J. Comput.-Aided Mol. Des. 2000, 14, 123-134
31. Kresse, G.; Furthmüller, J. Efficient Iterative Schemes for Ab Initio Total-Energy Calculations Using a Plane-Wave Basis Set Phys. Rev. B 1996, 54, 11169-11186
32. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
33. Kresse, G.; Joubert, D. From Ultrasoft Pseudopotentials to the Projector Augmented-Wave Method Phys. Rev. B 1999, 59, 1758-1775
34. Reckien, W.; Janetzko, F.; Peintinger, M. F.; Bredow, T. Implementation of Empirical Dispersion Corrections to Density Functional Theory for Periodic Systems J. Comput. Chem. 2012, 33, 2023-2031
35. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. A Consistent and Accurate Ab Initio Parametrization of Density Functional Dispersion Correction (DFT-D) for the 94 Elements H-Pu J. Chem. Phys. 2010, 132, 154104
36. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: New York, 1990.
37. Henkelman, G.; Arnaldsson, A.; Jónsson, H. A Fast and Robust Algorithm for Bader Decomposition of Charge Density Comput. Mater. Sci. 2006, 36, 354-360
38. Momma, K.; Izumi, F. Vesta 3 for Three-Dimensional Visualization of Crystal, Volumetric and Morphology Data J. Appl. Crystallogr. 2011, 44, 1272-1276
39. Kanai, K.; Ikame, T.; Ouchi, Y.; Seki, K. Molecular Orientation and Electronic Structure of 11,11,12,12-Tetracyanonaphtho-2,6-Quinodimethane Vacuum-Deposited on Metal Substrates: Charge Transfer, Complexation, and Potassium Doping J. Appl. Phys. 2009, 105, 023703-12
40. Smith, D. L.; Luss, H. R. The Crystal Structure of Bis(tetrathiotetracene) Triiodide, a One-Dimensional Organic Metal Acta Crystallogr., Sect. B: Struct. Sci. 1977, 33, 1744-1749
41. Beck, J. Ongoing work, 2013.